The usefulness of many pharmaceuticals and other biologically active agents, such as insect pheromones, depends critically on the fact that the molecules have a chiral atom of one specific chirality. However, any commercial synthesis of these compounds produces a racemic mixture of the compound produced with half the product of the desired chirality, and half of the opposite chirality. That is, when achiral molecules are resolved the two enantiomers are separated per chiral atom, each of opposite chirality. In commercial synthesis processes that utilize chiral allyl alcohols, the molecules whose chirality is opposite to that desired is of no use, and in some cases can be detrimental.
In a procedure described in Katsuki et al. U.S. Pat. Nos. 4,471,130 and 4,594,439 secondary allyl alcohols are converted from a racemic mixture to a single enantiomer of the desired chirality. This process is called Sharpless kinetic resolution. The enantiomer of the opposite chirality is converted to an epoxy alcohol whose carbinol carbon atom has the opposite configuration. This produces a substantially pure yield of the desired enantiomer, which amounts to about 50% of the racemic mixture. The other enantiomer, converted to an epoxy alcohol, may be of little value in the synthesis of a specific pheromone or other biological agent.